Than to Have Never Loved
by Aley Hock
Summary: Spin off of "Sometime No Means No". Dean's first love.
1. Chapter 1

I do not own anything, but Kripke did a fabulous job! The mistakes are mine however.

Dean Winchester sat in the front seat of his black '67 Impala, his little brother sitting in the seat beside him looking nervous. He could tell Sam was nervous because the kid had a death grip on the shoulder strap of his backpack, white knuckling it all the way. He has to chuckle to himself, only Sam would get himself this worked up about school.  
"Sam, relax man. Take a breath; we've been through this before." Dean soothes, squeezing the back of Sam's neck. But today was a big day for Sam; today was his first day of high school and the start of Dean's senior year. He was a mere ten months shy of graduating, ten unbearably long months. "This is the same song and dance that we've had to deal with our whole lives, right?" He shoots his kid brother a cocky grin and opens his door; Sam mirrors the lanky fourteen year old standing beside his brother taking the scene in. The school looked normal enough two hundred and some odd kids milling about, chatting up their friends. Dean takes a deep breath and pushes his little brother forward, following close behind towards the front of the school, they follow the signs to the main office, the secretary hands the boys their class schedules. It was time for the brothers to part ways, which was only making Sam that much more anxious. Sam was good at school, he unlike Dean liked school, but Sam was not good at making friends, making each new move that much more challenging.  
The boys go their separate ways, Sam shooting Dean one last nervous look and made his way down to the freshmen hallway. Dean saunters down the senior hallway scanning his schedule. 01 English 12 02 Physics 03 Government Lunch 04 Study Hall 05 Trig.  
06 College Preparation Not a bad load but what the hell is College Preparation, he thought to himself, looking up to scan the crowd of his classmates. They all looked fairly normal; the usual cliques were present jocks, nerds, stoners, and hotties. All of the girls were gorgeous, tall and lean. Especially the blonde, standing next to his assigned locker, she had great legs, tanned and toned, and an even better butt.  
Dean decided it was time to turn on that Winchester charm; he saunters up to her and gives her a cocky grin. "Hey Darlin'-"  
"Not interested," she sighs not even looking up, taking Dean aback. He never gets turned down. Most girls throw themselves at him. She glances over and sees Dean still standing there and smirks, "perhaps I was unclear when I said not interested I really meant was Back off." She clarifies bluntly, eyes blazing.  
"Um… I don't get it. Are you playing hard to get? 'Cause that's hot."  
She chuckles but in a snide way, "So it's gonna be like that, huh?" she muttered to herself. "Okay Romeo, here's the deal. In case my hostility wasn't a big enough red flag for you. I'm not some blonde bimbo that just blows a guy off to make them try harder." She takes a deep breath before continuing. "Now go away." She orders as she slams her locker door shut. Dean can't help but smile, this girl was full of piss and vinegar which made her all the more challenging. And there is nothing the Winchester men love more than a challenge. As the days and weeks progressed this challenge that Dean had set his sights upon was proving to be more difficult than he had expected. The leggy blonde he had set his sights on was not only immune to his charms but she was also the sheriff's precious baby girl, the only girl in a family of four boys. Katelynne Bree Moore or more commonly referred to as Katy Bree, was a force to be reckoned with, she was tough, smart, athletic. Everything Dean could have possibly wanted in the conquest of the month with one minor hitch; she wanted absolutely nothing to do with him. which in turn made him want her that much more. They had four out of his five classes together and she was always close to him, close enough that he could smell her shampoo and her perfume, Katy Bree smelt like magic. She was driving him crazy; what he wouldn't give to-  
"Dean!" John barked, his father's voice pulling him from his thoughts of Katy Bree Moore. "Huh?" Dean's head snapped up to meet John's dark eyes, quickly wiping a hand across his mouth, was he drooling? Get it together Dean; he thought to himself as John heaved an exasperated sigh.  
"I asked you if you noticed the impala was running a little rough, I think you need to check the timing belt." his dad scratched at his beard, John's menial patience nonexistence that afternoon.  
"Ya think so?" the old girl felt like she was running fine to him, but then again he'd been distracted lately. Dean cleared his throat before continuing "I'll take a look at it tomorrow after school, check things over."  
John gave what appeared to be a satisfied nod then asked, "Did you boys run this morning?"  
"No sir"  
Another nod from his dad, "alright well I'm going to go grab dinner, I want four miles from each of you before I get back, got it?"  
"Yes sir," Dean replied as he heaved himself up off the couch. "Sammy," he called "Quit playin' with your hair, we gotta train."  
A muffled "jerk" came from Sam's room as John went on his way to grab dinner for himself and the boys.

Dean Winchester was infuriating. Katy Bree Moore sat behind the counter of her mother's diner 'Moore Cookin', waiting for her chocolate crème pie to finish in the oven. Thursdays were chocolate pie day, since Katy was thirteen she had always made six pies on Wednesday night got up early the next morning and baked them for the dessert of the day. She hated Thursdays almost as much as she hated that cocky grin on Dean's smug face, and those perfect straight white teeth, his strong jaw, that leather jacket. He was a gorgeous infuriating man child.  
The shrill buzz of the timer interrupted her rant she scurried back to her pies, baked to perfection and pulled them out of the oven. She popped her head into her mother's office said her good byes and drove to school to being what was sure to be a long day. She just didn't realize how long until third period government. The senior project, a subject that sends a cold rush of fear in to the hearts of even the freshmen, every year the government classes are divided in to pairs, selected at random. Each pair is given a topic on which they are expected to write a 15-20 page paper. That paper is later converted in to a presentation in total said paper and presentation count for fifty percent of the final grade of the participants. Today was partner and topic assignments. Katy Bree sat there waiting for her doom to be handed down, and she had this horrible feeling that her day was only going to get worse.  
"Okay class now for the time you have all been wait so patiently for … project assignments. Girls you will pick the name of your partner unless I have told you other wise and gentlemen you will be picking the topic from the fish bowls at the end of my desk" Mrs. Jensen gestured toward the two bowls sitting on either side of her desk. "Now remember that I do not allow switching of partners or topics immediately following your selection you must come tell me what you have-" before she could finish her sentence Dean swung open the door and sauntered in to the class room, a whole forty-five minutes late. "Mr. Winchester, so nice of you to join us." grimaced Mrs. Jensen.  
Dean flashed her a cocky smile as he slid in to the seat behind me, I could feel his booted feet come to rest on the shelf under my seat that was meant for textbooks, "I had an opening in my schedule thought I'd swing by." He replied.  
Jensen rolled her eyes before continuing, "As I was saying you will report you partner and topic to me immediately after selecting them. I wish you the best of luck. You may begin." It was as if she had just told us to go swimming with Jaws, no one moved to do anything for a moment then slowly one by one their classmates began selecting their partners and topics. Katy Bree got up and made her way to the bowl containing names, she reached in and snatched one of the few remaining slips of paper. With shaky fingers she unfolded the slip and her heart literally stopped as she read the name scrawled across it.  
"You've got to be kidding me," Katy mumbled under her breath as she stood in line to tell her teacher who her partner would be.  
Jensen smiled excitedly, the woman far too happy to be inflicting pain and torture on her students. "Katy whom do you have dear?" she asked compliantly oblivious to Katy's dilemma.  
"Dean Winchester," Katy Bree sighed dejectedly, watching as his head snapped in her direction as he rooted around in the remaining topics. A sly smile crossed his face as he confidently snatched a piece up and walked a few steps over to her. Throwing an arm around her shoulders, Katy had to resist the urge to punch him where it counted.  
"Howdy partner," he greeted her as the bell rang dismissing them from class. Katy rolled her eyes and slipped from under his arm.  
"Don't forget I would like a rough outline for class tomorrow, nothing concrete I would just like for you to spend some time fostering comradely in this partnership being things on the right foot, have a good night see you tomorrow." bellowed Mrs. Jensen over the commotion of students packing up to go to their next classes. Dean smiled at her those perfect straight teeth sparkling, "So Katy Bree. When can I come over to your house?"  
She cut her eyes at him before saying, "Never, I work every day after school. Moore Cookin' you can meet me there at six when I have my dinner break. Some of us don't get to be delinquents all day."  
Dean looked insulted that she implied he was a delinquent, "I have a job thank you."  
"Oh yea where do you work, hoodlums are us?"  
He gave a forced laugh before shaking his head, "I take care of my little brother. Our dad's out of town a lot on business and leaves the kid for me to handle."  
"Where's your mom?" Katy asked, for the first time her tone was not full of disdain.  
Dean looked down at the floor, "My mom died when I was little."  
Katy Bree didn't know what to say after he dropped that bomb on her. Here she was thinking that Dean Winchester was some entitled punk, but that wasn't the case at all there was more to him than that façade he put on for the world to see, and yet there was still something dark, edgy just under the surface. "Oh, okay well I guess meet me at the diner at six and we can talk more about the project." She said this because how else do you reply to something like that? He gave a curt nod before leaving Katy by her desk alone to pull her foot out of her mouth.


	2. Chapter 2

Later that night Katy Bree sat waiting for Dean Winchester to show up. It was 6:20 and there was still no sign of him. She sat at the counter fuming that she hadn't thought to at least ask him what topic he choose so she could do some research of her own. Of all the seniors she could have been paired up with she had to pick Dean Winchester. The bell on the door tinkled it's song signifying that someone was entering the diner. Katy's head whipped around her eyes shooting daggers at the entrance, where Dean slunk in that tough guy swagger that he had radiating off of him like he was the sun. Any pity Katy Bree had mustered vanished the moment she saw his smug face.

"You're late," she growled as soon as he was within earshot, paying no attention to the scrawny shaggy haired kid that followed behind him.

"Yea well I got caught up with something, Katy this is my brother Sam, Sammy Katy."

A sly grin works its way on to the younger boy's face, "Oh so you're the infamous Katy Bree." Dean wasted no time in giving his little brother a silencing shove. "What?" the kid asked innocently.

"You know what, now quit bein' a punk and go do your homework." She heard Dean mutter to his brother, the older boy's cheeks tinging with just a bit of pink, as he pushed Sam towards one of the booths along the wall. "Sorry, the princess was late getting out of debate club and he hadn't eaten dinner so I couldn't just leave him to fend for himself, the kid can barely boil water. You understand." She nodded.

"Listen I've got to get back to it in like forty minutes so if you're done trying to dazzle me with these piss poor excuses, can we get started?" Katy Bree snapped slipping off the stool and leaning over the swing door that separated the restaurant and the kitchen to grab her back pack. Giving Dean a nice view of her butt, he barely had time to compose himself as she whipped back around nearly catching him ogling her. They made their way to the booth behind where Sam was working and began.

"Okay so what is our topic?"

Dean shrugged, "How should I know?"

Katy's eyes nearly popped out of her head, "You did pick a topic right? You were supposed to pick a topic. The girls picked the partner and the boys selected the topic, if you didn't pick a topic then we can't do the assignment and if we can't do the-"

"Easy killer, I never said I didn't pick a topic I just said I didn't know what the topic was." Dean pulled the slip of paper out of his pocket quickly flashing it for Katy to see. When she went to grab it he swiftly pulled out of reach.

"Dean!" Katy huffed.

"Katy honey, here is your dinner hot off the grill, your brother made it just the way you like it." a small blonde woman who resembled Katy a lot dropped a plate adorned with a cheese burger and fries. "Does your friend want something?" instantly Katy Bree exclaimed no as Dean said yes.

"Whoa, now hold your horses. I think that in order for us to be most productive we both need to be functioning to our highest potential; I can't do that on an empty stomach."

"And we cannot finish our outline if you don't work then I can't."

"Katelynne Bree Moore, I did not raise you to behave like this" Mrs. Moore turned back to Dean with a motherly smile, "What can I get for you, sugar?"

"I will take two of whatever she's having" Dean gestured towards Katy's plate. "One for me and one for my little brother, if that's alright ma'am." Dean drolled, laying the charm extra thick, "We are growing boys after all." He shot a glance at Sam who was busy working on his math homework; the kid was a giant bean pole.

Mrs. Moore beamed "So polite, Katy Bree this boy is a good egg I can tell." She patted her daughters head before heading back to the kitchen.

Dean leaned back in his booth and placed his arms behind his head, "Oh don't get so cocky just because my mother is completely oblivious to the fact that you are some sort of hell spawn does not mean I am."

"Well what can I say parents are not immune to my charms." a lopsided grin was shot at Katy.

"Shut up." she seethed picking up her burger and taking a bite of it, cheese oozed out of the center.

"Is that a juicy Lucy?" Dean asked a hungry look crossing his face.

"Why yes, yes it is. Doesn't it look delicious? Because it sure does taste that way." It was her turn to have a smug smile.

"That's just mean; you don't taunt men with food, that's practically cruel and unusual punishment."

"Well we all have to deal with hardships I'm dealing with one now." This comment received a chuckle from Dean as he slid the slip of paper over to Katy, his silent surrender in the battle of wits, conceding that for the moment they agreed to stop the bickering and attempt to get some work done.

Katy Bree and Dean began to make some real progress and once Mrs. Moore saw that she allowed Katy to continue working instead of making her go back to work. The Duo working till closing time as Katy's mother went to the office in the back of diner Katy got up and retrieved the reaming pie from the fridge in the kitchen. She got three forks incase Sam wanted to share with her and Dean and a can of whipped cream before heading back to the booth. Thinking that despite how much she had been dreading this group work it had turned out to be a good and productive night.

"I hope you plan on sharing." Dean smiled at her as she approached the booth.

"Share? This pie is all for me, if you want some you're gonna have to buy it. We aren't an organization to end hunger, but I may be able to be persuaded… with the proper incentive." Katy Bree though it was time for a little play back, she shot a quick glance at Sam who was passed out at his booth his face plastered to his textbook. She shook the can of whipped cream and began topping the pie. When she was done she scooped a finger full off and placed it in her mouth slowly sucking the dessert topping off. Dean's eyes fixed on her mouth; he scooted closer to her in the seat. Looking deeply in to her eyes a gaze so intense she almost had to look away.

"You've got some on your lips," he murmured inching closer, his full lips now mere centimeters from hers, "Don't worry I'll get it." he assured smiling further closing the space between them. She could feel the smoothness of his lips just brushing hers, his breath hot and sweet.

A gruff clearing of someone's throat puller her from Dean Winchester's trance, "Katelynne Bree, I think it's time for you friend and his brother to go home it's a school night." Her older brother Keegan snarled, eyeing Dean distrustfully. Katy swiftly slid out of her seat anxious to be away from Dean and the electricity she could feel between them.

"He was just leaving, right Dean?" prompted Katy giving Dean a wide birth so he could awaken his sleeping sibling and be on his way. And he did just that, after an intense stare down from Keegan, Dean shook his younger brother awake and they were on their way.

"I don 't like that guy," Keegan announced as he watched Dean and Sam drive away, a secrete smile played across Katy Bree's face as she thought 'yea I didn't either' as she began clearing the table of their remaining dishes and made her way to the kitchen.

"Don't worry Keegan; I can take care of myself." She told him as she passed, thought of seeing him tomorrow already giving her butterflies in her stomach.


	3. Chapter 3

Katy Bree could not sleep, her mind was running wild with all the possibilities that Dean Winchester presented. He was cocky, reckless, dangerous, a bad boy, the kind her mother had always told her to watch out for. And yet tonight she saw something else he was smart and funny, not at all like she had originally thought. He was all she could think about, that smile the leather jacket, those green eyes. Katy fell asleep imagining what it would be like to really kiss those lips.

Dean sat in the living room flipping through the television channels, not caring that it was nearly three o'clock on a school night. Katy Bree had been on his mind all night, their almost kiss leaving him unsettled The front door quietly opened revealing a weary John with an arm load of books. "Dean, son what are you doing up? You've got school in the morning; get your ass in bed. If I get a call from the school tomorrow you and I are gonna have a problem."

"Yes, sir." Dean murmured, "Hey dad?"

"What Dean?"

The blonde boy dropped his gaze to the floor, "Are we gonna be sticking around here for a while?"

"I don't know son, it depends a lot on what comes up in the next few weeks. Why, is your brother starting in on that crap already, he's doing that debate club-"

Dean quickly jumped to the defense of his little brother, "It's not for Sam dad…I don't know… I just kind of like it here… the school's not so bad and I'm even making some friends."

A concerned look crosses John's face, "_The schools not so bad?_ Are you sick…do you have a fever, because Dean Winchester hates school on principal." Dean scrambled away from John's looming hand.

"Dad I'm serious, I think I'd like to…I don't know… maybe stick around, you know; finish up the school year here." Dean admitted still refusing to make eye contact with his father.

John gave an exhausted sigh, "If this is really what you want, I guess we can see how things play out, I'll see what I can do." Dean beamed at him, "Now get to bed, you fall asleep in school and you won't have time to hang out with these friends 'cause you'll be training till graduation." John received a smile and a yes sir at that before Dean sauntered off to his room a little more pep in his step John's eyes watched his oldest son disappear in to his room, "Yeah, makin' friends my ass, more like making lady friends." John muttered to himself, walking over to the fridge and grabbing a beer before sitting in front of the TV, flipping through the channels before settling upon an old John Wayne movie letting his body relax knowing that all was well on the Winchester home front.

The Moore house hold was anything but peaceful the next morning. Katy Bree sat at the breakfast bar eating her usual morning breakfast, scrambled eggs two pieces of toast and turkey bacon watching the weather channel. All four of her brothers and her father milled about completing their morning rituals. The boys still lived at home, the twins Kory and Keegan worked in their mother's diner with Katy, and Kooper was one of her father's deputies. Then there was Kameron, who simply by the grace of God was able to graduate high school the year before and worked at the local mechanic shop across town. And despite them being of the male gender Katy Bree was convinced that they gossiped more than any girl she had ever met, they especially loved the topic of her and her life, that morning being no exception.

"So Katy, who this guy that was putting the moves on you last night?" asked Kory, Katy's.

Katy Bree leveled Keegan with a glare before moving to her next strategy, denial, "I don't know what you're talking about" she told Kory.

"Really that's not what I heard, little sister," interjected Kooper, the oldest child.

Katy forced a smile as she turned her attention toward Koop, "And what could you have possibly heard over the sounds of you and your sex monkey?"

A chorus of laughter came from all the boys not in her sights, "I heard you were playin' grab ass with some punk in one of your classes." Kooper snapped, not showing any mercy. That got her father's attention, his head snapping up from his newspaper so quickly she was afraid that he was trying to break his neck.

"You wanna repeat that Koop I don't think dad heard you clearly enough." laughed Katy's youngest brother Kameron as he stood up to rinse his dishes out in the kitchen sink, clipping Kooper's shoulder as he passed his older brother.

"Bite me Kam." Kooper growled turning on the younger giving Kameron a not so gentle shove and just like the focus was off Katy and on the quickly escalating fight.

"Hey," Mr. Moore barked, "It's too early for y'all to be starting crap, now Koop if you're going in with me you need to hull ass and get in the car I'm leaving whether you're in the car or not."

"I'll be right there dad." Kooper called to his father's back. "Kam, it's on when I get home from work tonight." another shove to his little brother's chest before storming out.

"Well who took a piss in his Cherries this morning?" Kameron muttered, just loud enough for Katy to hear before he playfully ruffled her hair, "Well, I gotta go to work I'll see you on the flipside." He smiled before bounding out of the kitchen leaving Katy with Keegan and Kory.

She glared at Keegan again, "Next time make sure you have all the facts before you go blabbing to the family chatty Kathy." she snarled taking her dishes to the sink.

"Well maybe if you and your new boyfriend didn't get it on in mom's restaurant then we wouldn't be having an issue."

Katy gave an exasperated sigh, "He's not my boyfriend!" she exclaimed as she stomped back to her room to get her things for school. Muttering to herself about stupid nosey big brothers and police officer fathers, before making her way to school and Dean Winchester.

"Dean get your ass in gear if I have to come back there and get you out of bed you're gonna be sorry." bellowed John, he had gone back to his oldest's room three times already in an attempt to rouse the teen.

On a normal morning the kid was a bear to deal with until he had caffeine now with only three hours of sleep John would be lucky if Dean made it out of bed in time for third period. The eighteen year old trudged out of the room to the bathroom where Sam was showering; John heard the toilet flush and Sam gave a surprise scream. "Dean," he howled, as the shower turned off and a towel clad Sam stomped out his floppy hair still sudsy. "Dad he did it again and now he kicked me out of the shower." whined the fourteen year old. Unfortunately Dean was not a morning person and with that came an extra dose of impatience that usually consisted of Dean kicking his younger brother out of the bathroom so he could shower by any means necessary. Lately that had been flushing the toilet turning the shower water frigid.

"Sam you'd been in the shower for twenty minutes, rinse you hair in the sink and get dressed you guys are gonna be late." ordered John pouring himself a third cup of coffee. Sam muttered to himself as he stuck his soapy head under the stream of the faucet rinsing the remaining suds out of his long hair. Once he was done he went to get dressed in his room.

Dean appeared a few minutes later hair damp shirtless in jeans as he began sifting through the dryer for a clean shirt, he found a well-worn black one pulled it over his head slipping his arms in the holes. He strode over to the coffee pot and filled a cup. He took a long drag before glancing at his father. "What?" he snapped

"Well first things first stowe the attitude, it's not my fault you decided to stay up till all hours second you've gotta stop interrupting your brother's shower, I will remind him of the time limit again but he can't keep washing his hair in the kitchen sink, okay?" Dean nodded, "Now get to school." John ordered as Sam came barreling out of the hallway backpack slung over his shoulder. "And try not to fall asleep again." He hollered to the boys backs, knowing he would most likely be getting a call that afternoon from the school.

School sucked, Dean thought as he fought to stay awake in _Physics _his father's warning echoing in the back of his mind. But hey at least he got to see Katy again in seventeen minutes, not that he was counting or anything. He just had to keep his eyes open for a few more minutes, it had been easy with her sitting right next to him in English, but now his eyes were just so heavy.

"Mr. Winchester!" Dean snapped to attention his head flying up from where he had laid it down, at his Physics teachers shrill voice, he couldn't have had been asleep that long he must have just drifted off.

For the life of him he could not remember her name, "Ma'am?" Dean scratched at his head attempting to bring himself to full wakefulness.

"Please try and stay awake for the last few minutes of class or there will be a detention in your future." she advised turning back to the chalk board.

Dean managed to stay awake the remainder of class and during government, they were on their way to lunch when they stumbled upon a small crowd at the center was none other than Dean's little brother getting the crap kicked out of him.

"Sam?" Dean shouted pushing his way towards his brother, pulling the mammoth sized football player off of Sam. "What the hell are you doing little brother, 'cause you sure as hell aren't fighting back." Dean gave the bully a solid shove and was all set to start throwing punches when Katy Bree placed a hand on his shoulder.

"Dean don't!" she exclaimed, in an attempt to contain his rage her hand had moved from his shoulder to his fist which was still balled in preparation for an ass kicking.

"Don't what? Fight for my family-"

"Take care of Sam now, fight for him later." Her eyes fell on Sam who was covered in blood.

Dean knelt in front of him, giving the kid a once over, "Looks like you were on the losing end of a fight with Apollo Creed buddy."

"More like a textbook." Sam mumbled leaning forward so that the blood streaming from his nose didn't run down his throat.

"Bruce Gill is a bully has been since kindergarten, he'll pick on anyone just for the heck of it." Katy explained, digging around in her back pack pulling out a pack of tissues. She handed one to Sam but Dean intercepted, snatching the tissue from Katy's hand, folding it in half then applying pressure to Sam's still bleeding nose. "Looks like you're going to have a hell of a shiner."

Dean took Sam's face in his hand, using Sam's chin to angle the boy's face from side to side. "So what happened?" he asked his little brother.

"Dumb ass is in my geometry class, the teacher told called him out told him I should tutor him, but she did it in the most embarrassing way possible, basically called him stupid in front of the entire class. He was pissed wanted to start a fight after class, when I didn't take the bait he clocked me with his history book."

"Yeah?" Dean asked helping Sam off the floor, "Well you have always had trouble with things hitting you in the face. You remember that time in Colorado, when we only had that old potbelly stove. We were getting wood for the night and dad tossed you a piece, you took your eye off of it for a second and BAM eight stiches, one black eye and a concussion later Dad was ready to skin you alive. 'Samuel get your head out of your ass and start paying attention or someone's going to get seriously hurt." Dean dropped the timber of his voice to do a gruff impersonation of John.

"Yeah, Dean I remember." muttered Sam blowing his nose in to the tissue.

"Or what about the time I knocked out your last baby tooth when we were sparing, Ooo or that time-"

Katy Bree stepped in "I think we get it Dean, Sam despite his very symmetrical face has a tendency of getting hit in the face with anything and everything." Dean shot her a pissy look before his attention went back to Sam.

"You're sure you're okay?"

To which Sam rolled his eyes, "Dean I'm fine. Relax, okay, this isn't the first bully I've dealt with. Go eat lunch, I'm gonna get cleaned up." Sam scurried away towards the bathroom and Katy and Dean went to eat their lunch.


	4. Chapter 4

Later that night Katy Bree was up to her eyeballs in the Friday night rush at the diner. It had been hectic since four thirty when the older regulars began coming in and now at eight thirty it was no calmer. The diner would be closed in an hour and a half and she could honestly say she was looking forward to it even Kory was looking a little worse for wear and his shift hadn't started till six. She had just finished dropping the bill at a table full of her father's deputies, when in strolled Dean and Sam Winchester, Sam now sporting more than a couple of bruises.

The hostess Nikki led them to Kory's section dropping sliver wear and menus on the table before returning to her post. Katy shot Dean a coy smile and gave him a small wave before she began bussing the table the officers had just vacated. Katy watched as Kory took their orders and she watched Dean help Sam with his math homework, Dean spent his time alternating between encouraging and teasing his little brother about being a geek. She picked up on bits and pieces of conversation each time she passed the brothers, her heart softening a bit more as she saw how Dean interacted with Sam. The brothers stayed till closing, and as Dean left she saw him slip a note on one of her tables, giving her a wink when he noticed her watching him.

Katy Bree sat in her car watching the clock as her curfew drew closer and closer. Dean's note had said to meet him in the park at 10:45 meaning she would have about an hour to hang out with Dean before she had to be home for the night. Her chocolate pie from the night before was placed on the seat beside her, as soon as all the tables were cleared and cleaned and Katy had swept her section she had left the restaurant. Explaining she was meeting a friend to hang out to her mother and slipping out before her brothers had caught wind of her plans. A bang on the passenger's side window sent a jolt of surprise down Katy Bree's spine.

"Hey sweetheart,' Dean smiled at her as he flung open the door.

It took Katy a minute to calm down, "Dean, that's not funny, you scared me." She scolded.

He gave her a less than remorseful look before sighing, "I'm sorry, I didn't mean to scare you." He leaned forward and switched off the radio that was playing a GooGoo Dolls song. "What the hell are you listening to?"

Katy slapped his hand away from the dial. "Don't insult my music choices, this band is awesome." She turned off her car, pulled the keys out of the ignition, and slid out from behind the wheel grabbing the pie before shutting the door to her car. She and Dean made their way to the swing set Dean still muttering about crappy boy bands.

Dean scoffed, "That band is crap, you want good music Metallica now that's an awesome band." He explained plopping down in one of the swings and turning towards her. "Journey, Queen, Styx, AC/DC, any of these ringin' a bell?"

Katy Bree giggled, "How old are you? I like music that is still relevant _today._"

Dean gave her a look of horror, "My music is relevant," he huffed, pouting like a little kid, "I have great taste in music." He muttered to himself kicking the ground as he began swinging with ease. "My mom used to listen to this stuff." He explained his eyes still trained on the ground. Then it all made sense, the dated music was one of the few pieces he had left of his mother. It was something that kept her memory alive. "She used to sing 'Hey Jude' to Sam when he was a baby… actually she used to sing it to me too, at night when I was hurt or scared or she was just trying to get me to go to bed and dad was working late-"

"You were stubborn even back then," Katy Bree laughed.

"Yeah well, being stubborn is a prerequisite to be a Winchester, hardwired from birth, just ask my little brother." A look of pride washed over Dean's face.

"You really love him don't you?" she asked.

"Yeah, I do," he replied without hesitation, "I mean I've practically raised the kid ya know. After mom died … I think it was too hard for dad… to…be there I guess. One day Sam's gonna be better."

"Better than what?" Katy asked studying Dean, "Better than you?"

"He's already better than me." Dean muttered, "Alright, enough of that crap, you are holding something that looks strangely like a pie."

Katy didn't want to drop the subject, but if stubbornness did run in the family she was not going to get very far by pushing him, "That is because it is a pie, the pie from last night to be exact."

"You brought me old pie?" Dean looked insulted.

"My pie is amazing even when it's a week old." She shot back raising a challenging eye brow. "But if you keep that up, you'll never get a taste." Katy Bree popped the lid off the pie and scooped up a slice with her hand passing it to Dean. He looked at it suspiciously taking a sniff before taking a tentative bite. His eye lit up with surprise.

"This is the best pie I've ever tasted." He exclaimed as he shoved the rest of the slice in his mouth.

Katy laughed again, "That is disgusting." Dean reached for another slice and she pushed herself just out of his reach. "No my pie deserves some respect."

He reached over grabbing the chain of her swing pulling Katy over to him. "I have the utmost respect for your pie." He murmured inching closer to her face.

She looked deeply in to Dean's green eyes the intensity of his stare leaving her breathless. "Is that so?" she whispered in his ear.

Her hair was tickling his face. "Yea that's so." He leaned away from her releasing the chain, sending her swaying back and forth. He saw her move out of his peripheral and come back in, he didn't see her hand coming towards the side of his head. The next thing he knew a cold gooey mass was slammed in to his face, the chocolate pie smearing in his hair and across his cheek.

She let out a hearty laugh, "Then have seconds please." She got off of the swing and sprinted across the playground. Dean caught up to her quickly slamming the remainder of the pie in to the back of her head. He made sure to rub it around and down her face. Both of them laughing like the teenagers they were, Dean relaxing enough to be a kid, a luxury he didn't often indulge in. Katy turned to face Dean both of them a mess of chocolate and whipped cream. Dean's face moving into Katy's space, his lips mere centimeters from hers, he had come 90% of the way hovering there, leaving the ball in her court. After a moment's hesitation he went for it first beginning with a gentle lead off peck then slipping a hand on the back of her head sharing a sweet chocolaty kiss. The warmth and the electricity they shared sending sparks between them. He kissed her deeply one last time before letting her go. Pulling away from her face, she gave him a sweet smile.

"Wow," she gave a breathy giggle.

"Yeah," Dean smiled stretching his arms over his head.

Katy glanced at her watch and frowned, "What's wrong?" asked Dean when he saw Katy's face fall.

"I have to go." She murmured, sneaking in for one last kiss, before scurrying off to her car, leaving him standing in the middle of the park hot and bothered and alone.


End file.
